Towards a rational design of molecular switches and sensors from their basic building blocks

Topics in Current Chemistry

Volumn 262, Issue , 2005, Pages 99-132

  Moonen, Nicolle N P ^a   Flood, Amar H ^a   Fernández, Juan M ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Kinetics; Molecular shuttles; Rotaxanes; Thermodynamics; Translational isomerism

Indexed keywords

EID: 33747586881     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_009     Document Type: Review

References (104)

1. Mendes PM, Flood AH, Stoddart JF (2005) Appl Phys A 80:1197
2. Huang TJ, Brough B, Ho CM, Liu Y, Flood AH, Bonvallet PA, Tseng HR, Stoddart JF, Baller M, Magonov S (2004) Appl Phys Lett 85:5391
3. Liu Y, Flood AH, Bonvallet PA, Vignon SA, Northrop BH, Tseng HR, Jeppesen JO, Huang TJ, Brough B, Baller M, Magonov S, Solares SD, Goddard WA, Ho CM, Stoddart JF (2005) J Am Chem Soc 127:9745
4. Nikitin K, Long B, Fitzmaurice D (2003) Chem Commun 282
5. Long B, Nikitin K, Fitzmaurice D (2003) J Am Chem Soc 125:5152
6. Nikitin K, Fitzmaurice D (2005) J Am Chem Soc 127:8067
7. Van Delden RA, Van Gelder MB, Huck NPM, Feringa BL (2003) Adv Funct Mater 13:319
8. Van Delden RA, Mecca T, Rosini C, Feringa BL (2004) Chem Eur J 10:61
9. Jiménez MC, Dietrich-Buchecker C, Sauvage J (2000) Angew Chem Int Ed 39:3284
10. Jiménez-Molero MC, Dietrich-Buchecker C, Sauvage JP (2002) Chem Eur J 8:1456
11. Jiménez-Molero MC, Dietrich-Buchecker C, Sauvage JP (2003) Chem Commun 1613
12. Sauvage JP (2005) Chem Commun 1507
13. Hernandez R, Tseng HR, Wong JW, Stoddart JF, Zink JI (2004) J Am Chem Soc 126:3370
14. Katz E, Lioubashevsky O, Willner I (2004) J Arn Chem Soc 126:15520
15. Katz E, Sheeney-Haj-Ichia L, Willner I (2004) Angew Chem Int Ed 43:3292
16. Luo Y, Collier CP, Jeppesen JO, Nielsen KA, De Ionno E, Ho G, Perkins J, Tseng HR, Yamamoto T, Stoddart JF, Heath JR (2002) ChemPhysChem 3:519
17. Huang TJ, Tseng HR, Sha L, Lu W, Brough B, Flood AH, Yu BD, Celestre PC, Chang JP, Stoddart JF, Ho CM (2004) Nano Lett 4:2065
18. Flood AH, Liu Y, Stoddart JF (2004) From cyclophanes to molecular machines. In: Hopf H, Gleiter R (eds) Modern Cyclophane Chemistry. Wiley, Weinheim, p 485
19. Flood AH, Ramirez RJA, Deng WQ, Muller RP, Goddard III WA, Stoddart JF (2004) Aust J Chem 57:301
20. Stoddart JF, Tseng HR (2003) PNAS 99:4797
21. Doddi G, Ercolani G, Mencarelli P, Piermattei A (2005) J Org Chem 70:3761
22. Diederich F, Stang PJ (eds) (2000) Templated Organic Synthesis. Wiley, Weinheim
23. Aricó F, Badjic JD, Cantrill SJ, Flood AH, Leung KCF, Liu Y, Stoddart JF (2005) Top Curr Chem 249:203
24. Koumura N, Geertsema EM, Van Gelder MB, Meetsma A, Feringa BL (2002) J Am Chem Soc 124:5037
25. Bottari G, Dehez F, Leigh DA, Nash PJ, Pérez EM, Wong JKY, Zerbetto F (2003) Angew Chem Int Ed 42:5886
26. Leigh DA, Wong JKY, Dehez F, Zerbetto F (2003) Nature 424:174
27. Hernández JV, Kay ER, Leigh DA (2004) Science 306:1532
28. Albrecht-Gary AM, Dietrich-Buchecker C, Saad Z, Sauvage JP (1992) Chem Commun 280
29. Leigh DA, Troisi A, Zerbetto F (2000) Angew Chem Int. Ed 39:350
30. Leigh DA, Troisi A, Zerbetto F (2001) Chem Eur J 7:1450
31. Odell B, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1988) Angew Chem Int Ed Engl 27:1547
32. Lu T, Zhang L, Gokel GW, Kaifer AE (1993) J Am Chem Soc 115:2542
33. Capobianchi S, Doddi G, Ercolani G, Keyes JW, Mencarelli P (1997) J Org Chem 62:7015
34. Kharitonov AB, Shipway AN, Katz E, Willner I (1999) Rev Anal Chem 18:255
35. Lahav M, Gabai R, Shipway AN, Willner I (1999) Chem Commun 1937
36. Lahav M, Shipway AN, Willner I (1999) J Chem Soc, Perkin Trans II 1925
37. Kaminski GA, Jorgensen WL (1999) J Chem Soc, Perkin Trans II 2365
38. Damgaard D, Nielsen MB, Lau J, Jensen KB, Zubarev R, Levillain E, Becher J (2000) J Mater Chem 10:2249
39. Zhang KC, Liu L, Mu TW, Guo QX (2001) Chem Phys Lett 333:195
40. Grubert L, Jacobi D, Buck K, Abraham W, Mügge C, Krause E (2001) Eur J Org Chem 20:3921
41. Hunter CA, Sanders JKM (1990) J Am Chem Soc 112:5525
42. Hunter CA (1993) Angew Chem Int Ed Engl 32:1584
43. Cozzi F, Siegel JS (1995) Pure Appl Chem 67:683
44. Shetty AS, Zhang J, Moore JS (1996) J Am Chem Soc 118:1019
45. Claessens CG, Stoddart JF (1997) J Phys Org Chem 10:254
46. Desiraju GR (1991) Acc Chem Res 24:290
47. Desiraju GR (1996) Acc Chem Res 29:441
48. Krishnamohan Sharma CV, Zaworotko MJ (1996) Chem Commun 2655
49. Steiner T (1997) Chem Commun 727
50. Berger I, Egli M (1997) Chem Eur J 3:1400
51. Bodige SG, Rogers RD, Blackstock SC (1997) Chem Commun 1669
52. Desiraju GR (1998) Top Curr Chem 198:57
53. Raymo FM, Bartberger MD, Houk KN, Stoddart JF (2001) 123:9264
54. Desiraju GR (2002) Acc Chem Res 35:565
55. Ashton PR, Odell B, Reddington MV, Slawin AMZ, Stoddart JF, Williams DJ (1988) Angew Chem Int Ed Engl 27:1550
56. Ashton PR, Goodnow TT, Kaifer AE, Reddington MW, Slawin AMZ, Spencer N, Stoddart JF, Vicent C, Williams DJ (1989) Angew Chem Int Ed Engl 28:1396
57. Raymo FM, Stoddart JF (2001) Switchable Catenanes, Molecular Shuttles. In: Feringa BL (ed) Molecular Switches. Wiley, Weinheim, p 219
58. Castro R, Nixon KR, Evanseck JD, Kaifer AE (1996) J Am Chem Soc 61:7298
59. Wudl F, Smith GM, Hufnagel EJ (1970) Chem Commun 1453
60. Philp D, Slawin AMZ, Spencer N, Stoddart JF (1991) Chem Commun 1584
61. Ballardini R, Balzani V, Dehaen W, Dell'erba AE, Raymo FM, Stoddart JF, Venturi M (2000) Eur J Org Chem 591
62. Collier CP, Mattersteig G, Wong EW, Luo Y, Beverly K, Sampaio J, Raymo FM, Stoddart JF, Heath JR (2000) Science 289:1172
63. Wong EW, Collier CP, Behloradsky M, Raymo FM, Stoddart JF, Heath JR (2000) J Am Chem Soc 122:5831
64. Collier CP, Jeppesen JO, Luo Y, Perkins J, Wong EW, Heath JR, Stoddart JF (2001) J Am Chem Soc 123:12632
65. Diehl MR, Steuerman DW, Tseng HR, Vignon SA, Star A, Celestre PC, Stoddart JF, Heath JR (2003) ChemPhysChem 3:519
66. Choi JW, Steuerman DW, Nygaard S, Flood AH, Braunschweig AB, Moonen NNP, Laursen BW, Luo Y, Delonno E, Peter AJ, Jeppesen JO, Stoddart JF, Heath JR (2005) Chem Eur J, accepted
67. Asakawa M, Dehaen W, L'abbe G, Menzer S, Nouwen J, Raymo FM, Stoddart JF, Williams DJ (1996) J Org Chem 61:9591
68. Anelli PL, Spencer N, Stoddart JF (1991) J Am Chem Soc 113:5131
69. Fyfe MCT, Stoddart JF (1997) Acc Chem Res 30:393
70. Bissell RA, Córdova E, Kaifer AE, Stoddart JF (1994) Nature 369:133
71. a determined by UV/Vis dilution studies in MeCN at 22°C. J Org Chem 66:3559
72. Córdova E, Bissell RA, Kaifer AE (1995) Potential vs. Ag/AgCl in MeCN. J Org Chem 60:1033
73. Balzani V, Credi A, Mattersteig G, Matthews OA, Raymo FM, Stoddart JF, Venturi M, White AJP, Williams DJ (2000) J Org Chem 65:1924
74. Anelli PL, Ashton PR, Ballardini R, Balzani V, Delgado M, Gandolfi MT, Goodnow TT, Kaifer AE, Philp D, Pietraszkiewicz M, Prodi L, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Vicent C, Williams DJ (1992) J Am Chem Soc 114:193
75. Córdova E, Bissell RA, Spencer N, Ashton PR, Stoddart JF, Kaifer AE (1993) J Org Chem 58:6550
76. a determined by UV/Vis dilution studies in MeCN at 21°C. J Org Chem 62:885
77. Mirzoian A, Kaifer AE (1995) J Org Chem 60:8093
78. Smitzrud DB, Diederich F (1990) J Am Chem Soc 112:339
79. Kosower EM (1958) J Am Chem Soc 80:3253
80. Reichardt C (1988) In: Solvents and Solvent Effects in Organic Chemistry, 2nd ed. Wiley, Weinheim, chap 7, p 339
81. Kang S, Vignon SA, Tseng H-R, Stoddart JF (2004) Chem Eur J 10:2555
82. Tseng HR, Vignon SA, Stoddart JF (2003) Angew Chem Int Ed 42:1491
83. Tseng HR, Vignon SA, Celestre PC, Perkins J, Jeppesen JO, Di Fabio A, Ballardini R, Gandolfi MT, Venturi M, Balzani V, Stoddart JF (2004) Chem Eur J 10:155
84. Tseng HR, Wu D, Fang NX, Zhang X, Stoddart JF (2004) ChemPhysChern 5:111
85. Flood AH, Stoddart JF, Steuerman DW, Heath JR (2004) Science 306:2055
86. Steuerman DW, Tseng HR, Peters AJ, Flood AH, Jeppesen JO, Nielsen KA, Stoddart JF, Heath JR (2004) Angew Chem Int Ed 43:6486
87. Flood AH, Peters AJ, Vignon SA, Steuerman DW, Tseng HR, Kang S, Heath JR, Stoddart JF (2004) Chem Eur J 10:6558
88. Jang SS, Jang YH, Kim YH, Goddard III WA, Flood AH, Laursen BW, Tseng HR, Stoddart JF, Jeppesen JO, Choi JW, Steuerman DW, Delonno E, Heath JR (2005) J Am Chem Soc 127:1563
89. Jeppesen JO, Perkins J, Becher J, Stoddart JF (2001) Angew Chem Int Ed 40:1216
90. Jeppesen JO, Nielsen KA, Perkins J, Vignon SA, Di Fabio A, Ballardini R, Gandolfi MT, Venturi M, Balzani V, Becher J, Stoddart JF (2003) Chem Eur J 9:2982
91. Jeppesen JO, Vignon SA, Stoddart JF (2003) Chem Eur J 9:4611
92. Jeppesen JO, Nygaard S, Vignon SA, Stoddart JF (2005) Eur J Org Chem 196
93. Laursen BW, Nygaard S, Jeppesen JO, Stoddart JF (2004) Org Lett 6:4167
94. Anelli PL, Asakawa M, Ashton PR, Bissell RA, Clavier G, Górski R, Kaifer AE, Langford SJ, Mattersteig G, Menzer S, Philp D, Slawin AMZ, Spencer N, Stoddart JF, Tolley MS, Williams DJ (1997) Chem Eur J 3:1113
95. Yamamoto T, Tseng HR, Stoddart JF, Balzani V, Credi A, Marchioni P, Venturi M (2003) There are indications for a folded conformation of the rotaxane in which there are π-π interactions between the TTF and the outer π-surface of the tetracation, see: Collect Czech Chem Commun 68:1488
96. Ashton PR, Blower M, Philp D, Spencer N, Stoddart JF, Tolley MS, Ballardini R, Ciano M, Balzani V, Gandolfi MT, Prodi L, McLean CH (1993) New J Chem 17:689
97. a) are both large and opposite in sign. In that, case, always very good population ratios will be found. The design of such a system would be a major challenge
98. Kramers H (1940) Physica 7:284
99. Grote RF, Hynes JT (1980) J Chem Phys 73:2715
100. Grote RF, Hynes JT (1981) J Chem Phys 74:4465
101. Sumi H, Marcus RA (1986) J Chem Phys 84:4894
102. Sumi H (1995) J Mol Liq 65/66:65
103. Ansari A, Jones CM, Henry ER, Hofrichter J, Eaton WA (1992) Science 256:1796
104. Jacob M, Greeves M, Holtermann G, Schmid FA (1999) Nat Struct Biol 6:923